Stroll to the center of the “Zona Colonial” to experience one of Santo Domingo’s liveliest outdoor scenes. Set in the vibrant heart of the historic district, Plaza España is a favorite gathering place for locals and visitors alike, who arrive as the sun sets to socialize and engage in people watching. The massive square, which offers splendid views of the Ozama River, often hosts folkloric shows and open-air music performances of jazz, rock and merengue. Many of the area’s top bars, restaurants, nightclubs and art galleries can be found on and around the communal space that’s been in use since the 1500s.

You’ll likely be drawn to one of the restaurants with spacious outdoor terraces that face the square. These eateries on the popular La Atarazana strip are housed in buildings dating to the 16th and 17th centuries. Settle down at a table to watch plaza life go by. Order a Mamá Juana like a true Dominican. The locally favored drink is a mix of rum, wine and honey that’s infused with herbs and tree bark. It’s a perfect companion for snacking on kipes, deep-fried balls of bulgur and seasoned beef. Save room for those yucca empanadas, stuffed with plump chicken and melted cheese. Perhaps you’ll top off the meal by lighting up a fine Dominican cigar as you take in the dynamic setting.

At night, lights create a picture-perfect scene on the square by illuminating one of Santo Domingo’s top attractions. A 16th-century palace that combines Moorish, Gothic and Renaissance architecture, the Alcázar de Colón was once the home of the son of Christopher Columbus. His father famously landed on the island in 1492 and is commemorated by a commanding statue on the plaza. Today, the structure is home to a collection of Medieval and Renaissance art, as well as period furniture that gives you an idea of what life was like in colonial days.

Amble across Plaza España to the riverfront Reales Atarazanas complex. A collection of buildings that dates to the 16th century, the “Royal Dockyards” were once a staging point for goods on the European trading route. After browsing the boutiques and art galleries that occupy the space today, you can learn about the region’s maritime history at the Museum of the Royal Shipyard. Why not end the evening with a nightcap? The plaza has a number of cozy bars that will be more than happy to serve you a rum drink in true local style.